Methyl 4-hydrazinylbenzoate → Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate

HRID 509719

반응식

HRID 509719 반응식
[NH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[NH2:2].Br[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[N:20][CH:21]=1>C(N(CC)CC)C>[CH3:22][C:19]1[N:20]=[CH:21][C:16]([CH2:15][CH2:14][N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)[NH2:2])=[CH:17][CH:18]=1

참가 물질

4

반응물 2

HCID 408928Methyl 4-hydrazinylbenzoateHCID 533058565-(2-Bromoethyl)-2-methylpyridine

생성물 1

HCID 68735268Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate수율 28.5%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Methyl 4-hydrazinylbenzoate (1 g, 0.005 moles) and 5-(2-bromoethyl)-2-methylpyridine (1 g, 0.005 moles) was taken up in triethylamine (2.1 mL) and stirred at RT for 1 hr. The reaction was heated at 100° C., overnight. LCMS analysis of the reaction mixtures shows the formation of product. The reaction mixture was concentrated, water (20 mL) was added to the reaction mixture and the mixture extracted with ethyl acetate. The crude product was dissolved in ethyl acetate and purified by column chromatography using neutral alumina, using 100% ethyl acetate as the eluent. After chromatography 400 mg of Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate was obtained, 28.5% yield.

후처리

  1. temperatureThe reaction was heated at 100° C., overnight
  2. customLCMS analysis of the reaction mixtures
  3. concentrationThe reaction mixture was concentrated
  4. additionwater (20 mL) was added to the reaction mixture
  5. extractionthe mixture extracted with ethyl acetate
  6. dissolutionThe crude product was dissolved in ethyl acetate
  7. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-c6ac98b775524cb3a8456186163c2323
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096591B2

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